The most valuable lessons in advisory work don’t come from the wins. They come from the moments that don’t go according to plan.
By Scott Gelbard, Founder — SGI Global Partners Inc. / Managing Partner — Peak Ventures
I want to be honest about something that doesn’t come up often enough in thought leadership circles: I have been wrong. More times than I’d like. About markets, about people, about timing, about which variables mattered most.
Twenty-five years into this work, I’ve stopped being embarrassed about that. Failure — properly examined — is the most reliable source of durable wisdom I’ve found in business. What I’m more careful about now is how I fail: whether I fail fast or slow, whether I fail forward or in circles, and whether I extract the lesson or just absorb the bruise.
Here’s what the past quarter-century has actually taught me.
Conviction Is a Tool. Stubbornness Is a Trap.
Early in my career, I mistook certainty for competence. If I’d done the analysis and reached a conclusion, I held that conclusion as a kind of professional identity. Changing my position felt like admitting error. So I’d hold on longer than the evidence warranted.
I’ve since learned to separate the two. Conviction — grounded in reasoning and updated by evidence — is one of the most valuable things an advisor can offer. Stubbornness — maintaining a position past the point where evidence supports it — destroys value silently and slowly.
The discipline I’ve built is this: whenever I hold a strong view, I force myself to articulate the two or three things that would change my mind. If I can’t name them, I’m not being rigorous — I’m being defensive. That single practice has saved me from some of my worst potential mistakes, and it’s saved clients from following me into them.
The Failures That Hurt Most Were the People Ones
I can look back at every significant setback in my career and trace it, if I’m honest, to a people decision — mine or the client’s. A wrong hire that stayed too long. A partnership pursued for strategic logic while ignoring cultural misalignment. A founder who said the right things in every meeting but had a different operating philosophy the moment pressure arrived.
Data, analysis, and frameworks are necessary. But they’re not sufficient. People execute strategy — or they don’t. And the qualities that matter most in execution — resilience, honesty, adaptability — are the ones that are hardest to assess in a due diligence process or a few months of advisory work.
I’ve become a significantly better reader of people over 25 years. But more importantly, I’ve become more honest about the limits of that skill. When I have a nagging doubt about a key person and I can’t resolve it analytically, I’ve learned to take that seriously rather than rationalize it away.
Failure at Scale Is More Expensive Than Failure at Seed
One of the cruelest dynamics in business is that the larger the organization, the more expensive it is to course-correct a flawed assumption. Companies that test small and learn fast — that treat early market entry or product launches as experiments, not commitments — suffer smaller failures that produce outsized learning.
I’ve advised companies that spent $20 million to learn something a $200,000 pilot would have revealed. The $20 million wasn’t wasted because the market was wrong. It was wasted because leadership treated uncertainty as a public relations problem to be managed rather than a signal to be studied.
The best risk management isn’t diversification or hedging. It’s building a culture that surfaces bad news early, takes it seriously, and responds before small problems become expensive ones.
The Stories We Tell Ourselves
The most dangerous failure mode I’ve observed — in clients and, frankly, in myself — is the narrative failure. We build explanatory stories around outcomes to make them feel manageable, and those stories protect our self-concept at the cost of accurate learning.
“The market wasn’t ready.” “We had bad luck with the macro.” “Our partner didn’t deliver.” Some of these are true. Many of them are partially true. Almost none of them are the complete story. And the parts we edit out are usually the parts that could actually make us better.
I’ve made it a practice, after every significant outcome — good or bad — to write a brief retrospective that specifically names what I’d do differently. Not what went wrong externally, but what I would change about my own judgment and decisions. It’s uncomfortable. It’s also the only post-mortem format that consistently produces something actionable.
What This Adds Up To
I’m a better advisor at 25 years than I was at five or ten — not primarily because I know more, but because I’ve failed more thoughtfully. I’ve built a set of mental disciplines forged specifically in the moments when I was most wrong.
The clients I serve best aren’t the ones with the cleanest stories. They’re the ones who’ve been through something hard and want to understand it honestly. Those conversations — grounded in real experience, not performance — are where the most valuable work happens.
Failure isn’t the opposite of good judgment. It’s the raw material.
About the Author:
Scott Gelbard is the Founder of SGI Global Partners Inc., a boutique family office and strategic advisory firm, and Managing Partner of Peak Ventures, an international business consulting practice. With more than 25 years of experience advising businesses across North America, Europe, and Asia, Scott specializes in market entry strategy, organizational resilience, and long-term value creation for entrepreneurial and family-owned enterprises.